These Are the Places I Will Always Go
by letters-from-London
Summary: AU. Blair is the hardworking girl from Brooklyn, Dan is the nice guy from the Upper East Side. The story takes place while they are in high school, and this is what happens when he goes to her for help with Serena. It's the story of Dan and Blair becoming friends, and eventually falling in love.
1. Chapter 1

As she began to stir from her sleep, Blair turns around to face the clock. 7:13. _Damn it. Not again!_ Blair thinks to herself as she shoots up from her bed. She has overslept once again, and only has seventeen minutes to get to the bus stop that will take her to school. If she misses this bus she will definitely be late for class, and she can't afford that. It is quite a commute from her family's loft in Brooklyn to Constance. Running around her room, Blair finds the remains of her uniform that she had thrown around the night before. Pulling her hair back with the first headband she finds and throwing on a pair of plain black flats, Blair runs out of her room. She is greeted with a silent apartment, with only the sound of the bustling city to wake her up. Grabbing an apple, Blair runs out of the apartment, and walks the few blocks to get to the bus stop. It is a beautiful, crisp fall morning. While strolling around the corner, Blair sees that the bus is already there and sprints forward to meet it.

* * *

"Good morning, son!" is the welcome that Dan receives as he joins his parents at the table for breakfast. His mom tries to make an effort to have the family eat one meal together a day, and because of everyone's busy schedules, breakfast is usually the only time that works. Dan scans the table. He sees a wide variety of different foods that he can choose from, depending on what he is in the mood for. He also sees that his sister is still not downstairs yet. Looking to his father, Dan mumbles a response groggily.

"Make sure you talk to your philosophy teacher about that grade you received on that test last week. If you can't get through to him I may have to make a call about it," Rufus tells his son.

"Don't worry, I'll take care of it today," Dan tells his him.

"Rufus, let's discuss that later. It's too early for conversations like that," his mother says.

Jenny then runs down the stairs. "Dan! We're going to be late! Come on; let's go down to the car now!" She grabs a bagel off the table and runs out the front door.

Dan stands and turns to grab his book bag. When he turns around, his dad is right behind him. Rufus takes Dan's tie in his hands and tightens it. "Remember, son, your future is in your hands. That's why it is imperative for you to talk to your teacher about that grade. If you can't get it up, then you can kiss your dream of going to Dartmouth goodbye."

Dan nods and steps away. His parents are always on him for something. They're pretty intense about matters concerning school. Rufus is a very successful music producer, and he used to be in a band. His mom is a famous artist with galleries all around New York City. With success in just the name of Humphrey, Dan is constantly feeling pressure about his grades and college.

Walking outside, Dan is greeted by the cool, fall air. He steps into the car, where Jenny is waiting for him, and they take off towards school. Jenny spends most of the ride chatting about insignificant things, such as the parties that are happening that weekend or some designer's new fall fashion line. He learned early in his life that sometimes it is just easier to tune her out and nod at the appropriate times.

When they arrive, Jenny immediately leaps up to join her friends that are waiting outside for her. Dan watches her walk into school surrounded by her group, who all seem to look the same to him. He will never understand what she sees in them because they all act like spoiled brats. Dan's family may have money, but he is anything but spoiled.

Dan walks across the street to grab his morning coffee. When he returns, Dan hears his name being called, and turns to find his friend Nate running towards him. Nate is his best friend and is the only person he has confided in about his family. He is the only one who understands how difficult family matters can be, probably because can identify with it. They smile at each other, and Nate claps his back. "Man! I didn't hear from you last night. How did your parents react to that grade?"

Dan takes a sip of coffee and responds nonchalantly, "Oh, you know, just the usual. 'I'm going to be a failure, a disappointment to the Humphrey name,' just the usual. I have to go talk to him before class starts, so I'm going to head in there now. I'll just meet you there?"

"Yeah that works. I see Chuck over there, and I've wanted to talk to him about this weekend anyways," Nate responds.

Dan winces. "God, I will never understand your friendship. He is a complete asshole to everyone, and a shitty friend to you."

Nate turns around and laughs back at him. They've had this argument several times before, and they never seem to get anywhere with it. Dan just shakes his head and goes to walk inside.

Without looking, Dan begins to walk up the stairs, only to find his feet fall out from underneath him. His coffee falls out of his hands as he tries to brace his fall. His hands catch himself from completely falling. All he can comprehend is an "oof" that he hears underneath him. Dan immediately springs up and looks down to see a very angry brunette with coffee all over her books and clothes.

* * *

_You have got to be kidding me._

"Watch where you're going, jerk!" Blair shrieks.

Blair had been relaxing outside on the steps with her book, waiting for her best friend to arrive. All she had wanted was some peace and quiet before her class began. Now, she has to deal with Dan Humphrey. Ugh, she was not anticipating this. Although they haven't talked in years, she knows him. Everybody knows Dan Humphrey. He is cute, smart, and his family is very wealthy. The girls at school talk about him all the time, so she knows more about him than she would like to. Blair stands up and turns to look at him.

"I am so sorry, I was not looking at where I was going…" Dan begins to respond.

Blair immediately interrupts, "No shit, Sherlock. God, now I have to wear this coffee-stained shirt all day. Thanks for that. And this book! I just got it yesterday! Wow, this day could not get any better."

"Listen, I really am sorry. It was an honest mistake. Is there anything I can do for you?"

Blair sighs. "No, it's fine. I've just had a crappy start to the day. I'll just head to class now, thanks for everything."

She begins to walk away, when Dan suddenly reaches out to grab her arm.

"You look really familiar. Do I know you from somewhere?" he asks her.

Blair laughs sarcastically and rolls her eyes. "No, we've just gone to school together for the past four years. I'll just go now."

She grabs her books and walks up the rest of the stairs, leaving a very puzzled Dan in her wake.

**A/N: Hey guys! So this is my first time writing fanfiction, so please review and let me know what you think! Constructive criticism is more than welcome!**


	2. Chapter 2

Blair stands in front of her locker, gathering her books for her first class, when Serena strolls over to her. Blair rolls her eyes and gives Serena an annoyed look. "Where were you this morning? I was waiting for you and you never showed up."

"Oh, I was just running late," Serena responds, "I got into _another_ argument with my mom. You know, just the usual thing."

There are many people at school who just do not understand the friendship of Blair and Serena. Serena has the all-American girl look that boys cannot seem to get enough of. She is popular, well connected, and her family has a lot of money. Blair, however, seems to be the complete opposite of her. Blair is beautiful, but in a more subtle way. She is hardworking, but things don't seem to work out as easily for her as they do for Serena. Plus, with Blair being from Brooklyn, she is often left feeling like an outsider. When word got out that Blair was only able to attend Constance because she received a full scholarship, her classmates scorned her even more than before. Considering all of their differences and very few similarities, most of their peers wondered how they were able to become such good friends.

Little do the people at Constance know, Blair and Serena have more in common than one would first think. When Blair walked in on Serena crying in an empty hallway their freshmen year, she was shocked at what she saw. Serena, the girl who always seemed to have it all together, was having a breakdown right in front of her eyes. When Serena looked up at her with red-rimmed eyes and mascara running down her face, Blair knew that she just needed someone to talk to. So, although they had never talked before, and Blair had heard all of the rumors about Serena being a complete bitch, she slid down onto the floor next to Serena. Blair looked through her purse and pulled out a wad of tissues and handed them to Serena. Serena laughed and took them, dabbing at her eyes. Serena told her about how she and her mom fought all the time and that they could never see eye to eye on anything. That morning they had a particularly bad argument and Serena could not seem to get over it. That was the moment that everything changed for Blair. For the first time in her life, Blair told someone else about the problems that she faced at home. A quiet loft, a mother who had no interest in her life, and the pressure and isolation that Blair faced every day at school. Blair told Serena everything, and she actually listened to every word that Blair told her. That day, Blair and Serena realized they had more in common than either would have thought, and that they could be the friend that each other had been looking for.

After that day, Blair and Serena became inseparable. They were best friends. When Serena was thrown out of her family's penthouse by her mom, Blair offered her loft for as long as she needed. Serena became an almost permanent fixture at the Waldorf's loft. Although Blair was embarrassed at first to have Serena over to her small Brooklyn loft, she was surprised to find that Serena loved it. Serena was enamored by how simply beautiful it was. And when Blair was harassed by their peers, Serena always stood up for her.

Their friendship first came as a shock, but now that they are both seniors, their classmates had gotten used to it.

So when Serena tells Blair that her and her mother were fighting, Blair gives her a sympathetic look and says, "I'm sorry, Serena. You'll get through it though, you both always do. You should just talk to her after school and try to work things out."

Serena nods distractedly, and then turns to her and spots the large coffee stain that is found on the front of Blair's shirt. Serena's eyes widen and she exclaims, "Blair! What happened to your shirt? Why didn't you say anything before?"

Blair rolls her eyes. "Dan Humphrey happened," she responds in a scornful tone.

"Dan Humphrey? Why would he spill coffee on you?" Serena replies while scrunching up her nose. "I have an extra shirt with me that you can use so you don't have to walk around with that stain all day."

"That would actually be perfect. And he didn't mean to, he just…" Blair begins to respond, but is cut short when Dan runs up to them.

"Blair! I am still so sorry about what happened earlier. But I got out of my meeting early, so I found my sister and asked her if she had an extra shirt. Turns out she did, so here you go," Dan says, and he pulls a shirt from his bag and hands it to her.

Blair looks at it and opens her mouth to respond when Serena interrupts and says, "Hold on a minute, I'm still lost as to what happened." She turns to Dan. "How did you manage to spill a whole cup of coffee all over her?"

"I was just sitting on the steps reading when Dan tripped…" Blair says at the same time that Dan begins to say, "I wasn't looking where I was going and fell over her..." They both continue telling the story from their different perspectives, and Serena just looks back and forth between the two of them, amused at the situation in front of her. She finally interrupts both of them and says, laughingly, "Alright, enough, I think I understand."

Dan tries to hand his shirt to Blair again, when she shakes her head and says, "Thanks so much for the thought, but I was actually planning on borrowing one of Serena's extra shirts."

He returns his gaze to Serena before saying, "Okay, well I need to head to class, but I'll talk to you both sometime soon." He turns to Blair and apologizes again.

"Really, Dan, it's fine now. I have to go change before class starts so we should go. Bye," Blair responds as she pulls Serena away and they walk down to Serena's locker.

Once they grabbed the shirt and Blair was able to change in the bathroom, they rush to their first hour class, which they conveniently have together. Serena slouches into her seat while Blair sits down and takes out her notebooks and a pen from her bag. Serena then turns to her with a big grin on her face and moves to whisper in Blair's ear. "Don't you think Dan is really cute?" Serena says quietly, but with a smile.

Blair looks at Serena with exasperation. "I thought you liked that guy from your English class!" Blair says. She never seems to get used to how quickly Serena moves on from guys. Even after the past four years, Blair is still surprised at how fickle Serena is with boys.

Serena gives her a look that makes Blair feel as if she missed something. "Blair, John and I are done, remember? Turns out we don't have anything in common. But Dan is like the complete opposite of him. He is such a nice guy, and it doesn't hurt that he is not lacking in the looks department!" Serena responds with a wink.

Blair just laughs and says, "I don't know, I guess he's just not my type."

* * *

After his morning meeting with his teacher, Dan trudged through his morning classes, waiting with anticipation until he can talk with Nate during their lunch hour. On his walk to find Nate, Dan starts to plan what he is going to tell his dad about his meeting. Rufus will be happy when he finds out the teacher didn't really argue with him about his grade. She was more than willing to help him out, even without the threat of his father. Sometimes Dan wishes that his teachers would argue with him instead of just giving him everything he, or more likely, his father, demanded. Sometimes he wishes that his last name didn't provide him with everything, and that he had to work harder instead of things just falling into his lap. But that's another mater that Dan had no control over. He enters into the cafeteria and looks for Nate. When Dan spots him, he notices Nate approaching him with a grin across his face. "Man, I heard about you spilling coffee all over that girl!" he says laughingly. "Nice going!"

Dan shakes his head and responds, "It was a complete accident. But there was something else I wanted to talk with you with about." Nate turns to him as they walk to their table to sit down. "What do you know about Serena van der Woodsen?" Dan asks with a smile.

Nate bursts out laughing and shakes his head. "More than you _know_! We grew up together, so she is basically my extended family. But now that we're older, I don't see her as much as I used to. Occasionally, our families will have dinner together, but that's basically it. Why do you ask?"

"I don't know, man. I think I might gather up the courage and finally ask her out. I have wanted to for a while, and I feel like now is the right time to do it," Dan responds.

"I think you should go for it," Nate says. "The only problem is that there are always rumors going around about how she moves quickly from guy to guy, so make sure you are careful about that."

Dan looks at him and says, "Yeah, but they could be just that, _rumors_. I want to know more about her. Plus, the other guys she has been with over the years have probably been jerks who did not know how to treat her right."

"Alright, I get it. So you should show her that you are different than the other guys that she may have been with. How are you going to manage that?" Nate asks.

Dan looks away and ponders his question quietly for a few moments. Then, he returns his gaze to Nate and says with a smile, "I need to befriend Blair Waldorf."

**A/N: So here is the second chapter! I hope you all enjoyed it! :) I know there isn't much Dair happening yet, but it will happen soon! I felt the need to provide some background for the characters first. Thank you to everyone who reviewed, you all are the best!**


	3. Chapter 3

After school, Dan takes his family's car back to the penthouse. He strolls into the foyer and is greeted by silence. But this is nothing new for him. His dad is always at the recording studio, and his mom tends to stay late at her art gallery. Jenny always has some social gathering to go to. But he doesn't mind it, Dan enjoys the quiet time to think.

He walks up the stair to his room and drops his book bag on the ground. Lying on his bed, Dan closes his eyes for a few moments. He thinks about his day, and realizes that he will have to talk to Rufus about the conversation he had with his teacher. His dad will be satisfied with the outcome, even if Dan is not. _Hard work will get you anywhere_ is his dad's mantra. From a young age, Rufus taught his children the importance of working hard and being independent. To make your own place in the world. However, Dan knows that he is just expected to follow in his father's footsteps. He is expected to work at Rufus' studio or possibly make his own business. Dan hops off his bed and heads over to his bookshelf and grabs the notebook that he hides between all of his school books. He sits at his desk and opens it to the next blank page. _If only my parents knew my real passion was writing._ He laughs to himself just thinking about what their reaction would be to this news.

As much as his parents talk about the importance of creating your own path, they sure are close-minded about what that path should be.

* * *

Blair rushes back to the loft after her last class. "Mom, I'm home and heading to work!" she calls as she runs into her room to change. All throughout high school, Blair has worked at The Coffeeshop Around the Corner, which is an adorable little coffee house a few blocks away from her home. Even though it can be hard to balance school and work, the Waldorf family needs the extra money.

After changing into her work uniform, Blair walks into her mom's room to check on her. Her parents' divorce had a really harsh impact on her mom. Eleanor once had dreams to become a fashion designer, but after the separation, she lost all of her inspiration and motivation. Now she works random, odd jobs just to be able to make the rent. And if Eleanor isn't working, she stays in her room, quiet and alone.

Thank god for the check her dad sends every month and the money Blair makes at The Coffeeshop Around the Corner. Or else they would have had to move into an even smaller place years ago.

Blair walks in to see her mom lying in her bed. "Hey mom, I'm just heading to work. I won't be back until later though because I have the late shift."

Eleanor turns to Blair and responds, "Okay, honey. I'm working the night shift, so I probably won't see you until tomorrow, or maybe the day after."

"Bye, mom," Blair says as she leaves. She often wishes she was able to talk to her mom about the things that happen in her life. They rarely even have time to say hello anymore. If Blair didn't push her mom to find jobs and actually go to them, Eleanor would probably just lay in bed all day. Sometimes she wishes she had Serena's mom as her mom. Even though they fight all the time, at least Mrs. Van der Woodsen cares about _something_.

Blair worries constantly about how her mom will be when she leaves for college next year.

She steps outside and begins to walk down to the coffee shop. It is only a twenty minute walk, and it's a nice walk that she usually spends clearing her mind. _Work. College applications. Homework_. Those are the things running through her mind on her walk. _It's going to be a very late night for me tonight_ she thinks to herself.

When Blair arrives to work, she punches in and puts on her black apron. Then she steps in front of the register to help the next customer. "Welcome to The Coffeeshop Around the Corner! I'm Blair, what can I get for you?"

* * *

Blair leans against the counter, taking a break after working for a few hours. The bell rings, signaling the arrival of a new customer. Blair looks over to the door and watches Vanessa walk in. Blair smiles and says, "Hey girl! I haven't seen you in a few days." She begins to make Vanessa's drink. She always gets the same thing whenever she comes to visit Blair.

"I know, I've been so busy with school. I miss you! How has everything been going?" Vanessa responds with a grin.

"Oh, you know, just the usual. I've been working a lot though. I need to start saving as much money as possible so I can afford to go to Yale next year. That is, if I even get in," Blair responds with a nervous shake of her head as she continues to brew Vanessa's coffee.

"Blair, Yale has been your dream school since you were a kid. I even remember you telling me when we were _six_ that you were going to go to college there when you were older. You work harder than anyone I know. Yale would be crazy not to accept you!" Vanessa tells her.

"Thanks, you always were good at keeping my spirits up! I just haven't been able to spend as much time on my application as I would like to, so I guess I'm just nervous. Plus, I am just really exhausted, I haven't been sleeping much lately," Blair says as she hands Vanessa her drink.

"I really think you should talk to your mom about this. You are working yourself into the ground. It's not fair for you to have to work this much, and balance school, and have to worry about college applications. Blair, just talk to her…" Vanessa trails off as Blair silences her with a look that could kill.

"That is out of the question. But thanks for the thought, Vanessa. Now go relax with your drink. It's on me," Blair says with a wink.

"Oh, you don't have to do that! I really just came to see you. I haven't been able to talk to you in a while."

"I know, but I want to give you some incentive to come visit me some more!" Blair responds with a laugh.

Vanessa ended up staying an hour, and when she left Blair began to clean up the coffee house for the evening. When ten o'clock hit, Blair changes the "open" signed to say "closed," and locks the door. She begins her walk home. Blair crosses her arms, wishing she brought a jacket. The temperature cools off considerably in the fall. When she arrives home, she sees that her mom is gone. Blair walks into her room and changes into her pajamas. Climbing into bed, she grabs her books and settles in for a late night.

* * *

The next day at school, between class periods, Dan approaches Blair at her locker.

"Hey Blair, how is your day going?" Dan asks her brightly.

Blair shoots him a look and responds with a smirk, "Oh, it was going great until now."

Dan throws his head back and laughs. His laugh is contagious and next thing she knows, Blair is laughing along with him.

"Okay, listen. There is something I wanted to talk to you about. Do you have a free minute right now?" Dan asks her.

Blair sighs and says, "Fine, you can walk with me to my next class." She grabs her books and starts walking away, leaving Dan to catch up with her. "This better be worth my time," she says, turning to him. "There are other things I could be doing right now."

"What else would you be doing right now?" Dan asks her with a questioning look.

"Not talking to you," she responds with a smile.

Dan just shakes his head with a slight smile. He turns to her and says, "I need your help, Blair."

"My help? With what?! You didn't even remember my name yesterday! How could I possibly help you?" Blair responds with an annoyed tone in her voice. They arrive at her class and she turns around to face him.

"I was thinking of asking Serena out on a date…" Dan begins but stops when he sees Blair roll her eyes and turn to walk into her classroom. "Wait! Where are you going? I haven't even explained anything yet!" Dan exclaims exasperatedly.

Blair turns back to him angrily. "Do you know how many guys have been interested in Serena? And how many guys have broken her heart over the years?! Too many to count. And I'm always the one to pick up the pieces they leave behind. So sorry if I'm not exactly supportive of you."

"I've heard about the other guys. I'm just trying to tell you that I'm different," Dan says, shaking his head. "I'm already trying to show you that I'm different than the others. I'm talking to you about it. I'm sure the other guys didn't even try to get to know you. And you're her best friend! I want to get to know you!"

"So you just want to become friends with me because of Serena?" Blair asks, obviously annoyed.

"No, no. God, this isn't coming out right," Dan says, shaking his head. "I keep putting my foot in my mouth." Dan takes a deep breath. "I want to be friends with you. But maybe you could also help me out with Serena."

Blair looks at him for a moment. "And what would I get out of this?"

"I would treat your best friend as she deserves to be treated. You could see her be truly happy," Dan responds.

Blair looks at him for another minute, then glances at her watch. "Look, I have to get to class. Can I think about it?"

"Yes! Yes, of course!" Dan exclaims. "Look, I'll give you my number so you can call me whenever you make up your mind."

* * *

"… so then he grabbed my notebook and wrote his number in it! And now I don't know what to do! What do you think?" Blair asks. Vanessa came to visit Blair again at the coffee shop and Blair retold the entire story to Vanessa.

Vanessa is quiet for a moment, then looks up and asks her, "Are you ever sick of standing in Serena's shadow? You do so much for her, and it seems like she never does anything for you. You deserve better than that, you know."

"Not this again! I understand where you're coming from, I really do. But you don't understand how much we've been through together," Blair responds. They've had this argument many times before. Vanessa and Serena are not the biggest fans of each other, which often puts Blair in an awkward situation.

"Okay fine! I'm just saying, you do a lot for her. Maybe instead of helping her get with this nice guy, who she will obviously date once and then find a new guy to obsess over, you could spend the time on yourself. Maybe you could even find a nice guy for yourself," Vanessa responds.

Blair laughs at that. "Oh yeah, with all of the free time that I have! We'll see. I haven't decided yet to do about Dan. I'll try to figure things out before tomorrow, I guess."

After work, Blair walks home contemplating what to do about Dan and Serena. It would be nice to see Serena date an actually nice guy. Most of the boys she has dated have been complete assholes from the beginning. Maybe Dan will be different. But Vanessa was right about something. It is difficult to live in Serena's shadow, so maybe she should just leave the situation alone.

Later, as Blair is doing her homework, she comes across Dan's number that he scribbled in her notebook. She looks at it for a moment, then picks up her phone. _It's really late, so he is probably already asleep. I could just leave him a message._ She dials his number and listens to the line ring several times, then Blair hears Dan pick up.

"Hello?"

"Hey, Dan. It's Blair. Blair Waldorf. If the offer still stands, I can help you."

**A/N: Hello again! Thank you so much for all of your reviews! Thanks to starry for your review! You were extremely helpful! :) **

**Please continue with the reviews! And enjoy the rest of your day!**


	4. Chapter 4

The rest of the week passes by in a blur for both Dan and Blair. Friday after classes, Dan approaches Blair as she is getting ready to leave. "Hey, Blair! So I was wondering if you were free at all this weekend. Maybe we could meet up and hang out or something?" he asks her.

Blair looks up at him and responds, "Well, I'm working basically all weekend and any free time that I end up having I will be working on my college applications. So I'm not sure when we would be able to."

"Where do you work?" Dan asks as Blair closes her locker and begins to walk outside.

Opening the doors and walking into the beautiful fall New York day, Blair turns to him and answers, "It's called The Coffeeshop Around the Corner. It's a small coffee house in Brooklyn."

Dan stops and turns around to answer her when he realizes that she has kept walking away from him. "Hey! Where are you going?" he yells to Blair.

"I need to go now so I can make the bus to take me home. I can't miss it or else I will have to wait for another hour and then I'll be late for work!" she yells back to him.

Dan runs up to her and says, "Hey, I can give you a ride home if you need one. I have my family's car here and nowhere to be, so I wouldn't mind driving you home. Plus public transportation is disgusting."

Blair shakes her head and responds, "There's no way. I live all the way in Brooklyn!"

"I'm not taking no for an answer. Plus, you'll probably get home even faster than normal. Let's get going!" Dan says as he ushers Blair into the car.

She sighs exasperatedly and says, "This is not going to become a regular thing. I am fully capable of taking this 'disgusting' public transportation that you speak of. I have been taking it for years!"

"Yeah, yeah, I get it. Let's go so we can get you to work on time!" Dan says as he closes the door after Blair.

Walking around the car, Dan opens his door and steps in the car. After sitting down, he turns to Blair and says, "You can tell the driver your address."

Blair whispers _I cannot believe this_ to herself as she turns to the driver and tells him where she lives.

As the car begins its route to Brooklyn, Dan turns to Blair and asks, "So what schools have you been applying to for next year?"

Blair smiles to herself at the safe subject matter that he has decided to talk about. "Well, my dream school has always been Yale, so I've put most of my time in that application. But I'm also applying to Columbia in the city and Harvard. I'm still working on all of my applications though. It's hard to find time for them between work and school."

Dan considers her answer for a moment before responding. "I'm also applying to Columbia, but I'm hoping for Dartmouth. Applying to schools is stressful though. I've dreamed of Dartmouth my whole life, and it's scary to think that I may not even be accepted."

"I'm sure if Daddy pays the right price, you can go anywhere you want," Blair responds with a smirk.

Dan rolls his eyes and shoots her an annoyed look. "It's actually not that way at all. I _cannot stand _when people say that. I have to work hard for my future also, just like you," he says.

"Yeah, but even if I get into Yale, there's no way I could even afford it. So you actually don't have as much to worry about as you think you do!" Blair exclaims.

Dan stares at her for a moment, and then says, "Look, you don't know anything about me. So you can stop…" before Blair interrupts him with, "I know more about you than you think."

They stare at each other without saying anything, both of them too stubborn to break eye contact. Eventually, Dan looks away and says, "You know, I actually do want to be friends with you. But this isn't going to work if you don't want it either."

Blair sighs and responds, "I know, I'm sorry. I don't really think before I talk."

Dan laughs and says, "It's alright. We'll work it out. And just for the record, I may not have to worry about financial problems, but I do have other things going on that I do have on my mind. Money doesn't solve all problems."

"I'm sure. Sorry for completely judging you by what I've heard. I usually don't act this way, but I think all this stress has gotten to me," Blair responds.

"You're fine, really. It's actually refreshing to talk to someone who doesn't hide her thoughts," Dan says.

The rest of the car ride is spent in companionable silence. When they arrive at her loft, Dan rushes out of the car to open up Blair's door. "Well, I guess chivalry isn't dead," she says as she steps out of the door. Dan responds with a mocking bow, which makes Blair laugh.

"Okay, so I work tomorrow from seven in the morning until closing, but I have a break from noon to one. So feel free to stop by the coffee shop anytime tomorrow," Blair says as she walks to the front door.

Dan waves goodbye and says, "Alright! Well I will see you sometime tomorrow."

Blair waves back and walks inside. She climbs the stairs up to her loft and goes into her room. _Wow_, she thinks to herself, _I got home so much quicker than I usually do! This is really nice._ With the extra time, Blair was able to lie down for about twenty minutes before she changes into her uniform, leaves her loft, and makes the walk to work.

* * *

_I spend too much time here_ Blair thinks to herself as she leans against the counter at The Coffeeshop Around the Corner. She sighs and runs her hand over her face.

"Blair! You can go on break now. Be back in an hour!" her manager yells to her.

"Finally," Blair grumbles to herself. While her usual cup of coffee is brewing, Blair runs in the back to grab her book and brings it up front. When her coffee is done, Blair grabs it and her book and sits down on one of the couches.

Not too much time later, Blair hears, "_The Age of Innocence._ Good, but not one of my favorites." Blair looks up to see Dan smiling right in front of her with a cup of coffee in his hands.

"Oh, really? And what would be your favorite?" Blair asks him with a sarcastic tone as she closes her book.

"Oh, I'd say I'm more of a fan of Chad Harbach," Dan responds as he sits down in the seat next to her.

Blair scoffs and says, "Chad Harbach? Do you not have any taste in literature at all?!"

"Hey now! No need to trash Harbach. We can have this conversation another time. I wanted to come visit you during your break to talk about this deal with Serena. How much time do you have until you have to go back?" Dan asks.

"I have about forty minutes left, so let's get this over with. So Serena. Do you have any ideas at all? When do you want to talk to her?" Blair responds.

"I was thinking sometime this weekend. And I was just thinking of going to her home and giving her the classic bouquet of roses," Dan says nervously.

Blair rolls her eyes and says, "No, simple and sweet does not work with Serena. Did you hear anything about Jackson? Or Simon? They were Serena's most recent boys." Dan shakes his head. "Okay, well Jackson took Serena on his family's yacht for their first date, and Simon showed her his family's house in the Hamptons. And neither of them got the pleasure of a second date with her. Your family has money, so I suggest you put it to use for her. Try to think of something creative, something she has never done before."

"I haven't even thought about our first date, Blair, I'm still trying to think of how I'm going to ask her out! She may not even say yes!" Dan says exasperatedly.

"Oh, please. She's going to say yes. And I think the flowers are a good idea. Most of the other guys just texted or called her to ask her out. If you do it in person, she could see the effort that you're putting in and that you're different than the other guys she has been with," Blair responds as she takes a sip of her coffee.

"Okay. And does Serena really put that much priority on money? Because most of the things I like to do don't necessarily cost money. So I'm going to really struggle to come up with ideas for a date," Dan says as he laughs nervously.

Blair looks at him for a moment with a contemplating look before replying, "Don't worry, if it's meant to be it will happen. Plus, I'll put in a good word for you," she says with a wink.

Dan laughs and says, "Thanks, Blair. For everything, you truly have been a big help."

"It was my pleasure," Blair says with a smile.

They spend the rest of their time together talking about little things. Dan asks her about her day, and she tells him a story of an old man who yelled at her earlier that morning, which made them both laugh. Dan tells her about his family brunch, which turned into a disaster because Jenny came down hungover, and his parents yelled at her the whole time about responsibility. The story made Blair shake her head at the ridiculousness, because she had never needed to get that speech from her parents. Before either of them knew it, one o'clock came around and Blair had to go back to work.

"Well it was a pleasure not spending time with you," Blair says to him with a smile.

Dan laughs and says, "Let's not do it again sometime. Bye, Blair. Thanks again for your help, and I'll see you at school on Monday."

"No problem, Dan. And good luck!" Blair yells to him as he walks out of the door. He turns back to wave at her once more before turning to walk to his car.

The rest of the day passes by in a blur for Blair. She only has one thought on her mind, and that is how easy and right it felt to spend time with Dan.

* * *

The rest of the weekend passes by uneventfully for Blair until Sunday night. Blair has Sundays off work, so she spent most of her free day catching up on homework and working on her college applications. She is lying down on her bed when she gets the call from Serena. Blair sighs, picking up her phone. Deep in her chest, Blair feels a pang of hurt and jealously, before quickly ignoring it and putting it away._ You knew this was coming. Don't act so surprised_ Blair thinks to herself.

Blair answers the phone and says brightly, "Hey, S! How's it going?"

"Blair!" Serena screams over the phone. "You'll never guess what just happened! Dan Humphrey asked me out! DAN HUMPHREY! Can you believe it?! And be bought me flowers and everything!"

Blair paints a smile on her face and tries desperately to sound happy for her friend. "Serena, that's wonderful! But I already knew! Dan approached me earlier this week about it. He is a really good guy for you, S. I'm beyond happy for you!"

"Oh you are the greatest friend a girl could ask for! I've actually got to go, though. I just thought you should be the first to hear about it! Love you girl, and I'll see you tomorrow!" Serena says as she hangs up.

"Bye, Serena," Blair says to the dial tone.

She puts her phone away and sits in silence for a moment._ Dan Humphrey is just a friend. No, I can't even call him a friend yet. Dan Humphrey is just an acquaintance _Blair tells herself. Yet, she was still unable to get that heavy feeling off of her chest.

**A/N: Hey guys! So here is the next chapter! The last few chapters I haven't gotten as many reviews or hits on the story, so I'm not sure if I should continue with it. So please let me know if you want me to finish it! I have the rest of it outlined, so it would just be a matter of finding time to write the rest of it if you guys want to! Sorry for the long message, but I hope you enjoyed the new chapter! :)**

**I'm also posting the link to my new tumblr on my profile! I will post it there each time I have a new chapter!**


	5. Chapter 5

The next week at school, Dan decides to talk to Blair again about his plan for his and Serena's first date. He decides to talk to her during lunch. When he walks into the cafeteria, he sees her sitting by herself, reading a book. He smiles and walks over to her, purposefully crashing into her when he sits next to her.

"God, Dan! Look where you're going! I could have spilled my lunch all over myself!" Blair yells at him.

Dan laughs and says, "I just couldn't resist. You looked so quiet and peaceful! Do you do anything else in your free time besides read?"

"Not really. There's nothing I enjoy more than curling up with a good book. Besides maybe an Audrey Hepburn movie," Blair responds.

Dan crinkles his nose and says, "Audrey Hepburn? I don't know about her, but I am a fan of the classics. We should watch one of her movies together sometime. And I also love to read. That's something we have in common," he says as he bumps shoulders with Blair.

Blair just laughs and says, "I'm sure we have more in common than we think we do. So why did you come over here?"

"Can't I just come over here to say hello?" Dan responds in a condescending tone. Blair shoots him a look, which makes him look at her sheepishly. "Actually, I was wondering if I could talk to you about my date with Serena?" he asks hopefully.

Blair sighs, closes her book, and puts it in her book bag. "Go ahead. What's your plan?"

Dan grins and asks, "Well, you know my dad owns his own musical production company?" Blair nods. "Well, one of his clients, Vampire Weekend, is in town this weekend. I have two VIP passes, and I was thinking of surprising her with the tickets after I take her to dinner. So… What do you think?"

Blair is quiet for a moment while she thinks. Then a smile spreads across her face. "Serena loves concerts," she says as she looks over to Dan.

Dan smiles and leans back, looking as if a weight had been lifted off his shoulders. "Thank god," he says, "that was my only idea! Thank you so much for your help, Blair. Truly, you're the best."

Smiling, Blair says, "Anytime."

They spend the next few minutes talking about insignificant things, before Dan spots Nate across the room and leaves to go talk to him. Blair watches him leave, with that same heavy feeling in her chest.

* * *

The end of the week finally comes, and as Blair is packing up her things before she leaves for the bus, Serena approaches her and says quietly, "Blair, I don't know how I feel tonight. I'm getting really nervous, and I don't get nervous before dates. What do I do?! Part of me just wants to call this off."

Blair gives her a disbelieving look before saying, "Don't you dare! He is so excited about tonight. Plus, he told me what he was doing with you, and you'll love it! It will be so much fun. Don't even think about not going." Blair looks at Serena, contemplating. "Maybe you're just nervous because this is the first gentleman you have ever dated. Dan is obviously different than the other guys you've dated, and that could be freaking you out."

Serena gives her a sheepish smile and says, "How did you know? I'm just worried. What if his nice guy act is just that: an act? What if he tries something?"

Blair gives her an incredulous look and says, "You have got to be joking. Dan is the last guy who would ever try something like that." She has a slight smile as she says, "I've actually gotten to know him these past two weeks, and he truly is a good guy. You have nothing to worry about."

"Do you really think so?" Serena asks with a hopeful smile, which Blair responds with by nodding. "Okay, thank you so much, Blair. You always know the right thing to say!" Serena throws her arms around Blair and gives her a hug. When she releases her, Serena says, "Okay, well I am going to go home and get ready for tonight. I'll call you after I get home! Will you be home from work by then?"

"I should be! And you better call me after! I can't wait to hear all of the details from you!" Blair says. She looks down at her watch. Realizing what time it is, Blair grabs all of her stuff and starts running down the hallway yelling back, "Shit! I'm going to miss my bus! I need to run, but call me later Serena!"

Serena nods and waves back, turning around to go back to her home.

* * *

Dan sits down on his couch with Nate next to him. Nate turns to him and says teasingly, "So, are you ready? Tonight is a big night for you, man! You've been waiting for this for a while."

Dan rolls his eyes and says, "Come on. I didn't wait that long!"

Nate laughs and responds, "It took you a while to gather the courage to do it. But I give you props, I haven't gotten the courage to ask anyone on a date in a while."

"Is there anyone that you've had your eyes on lately?" Dan asks him.

Nate thinks quietly for a moment before laughing lightly and responding, "I'm not sure yet. But you'll be the first person I talk to about it though, don't worry! Now what do you say we grab some coffee before you head out on your date?" he asks lightly.

"Now that is an idea that I fully support," Dan says. He grabs some money before he and Nate leave the apartment with their jackets in their arms.

* * *

Blair runs out of the school and doesn't stop until she gets to her bus stop. When she arrives, she realizes that she missed her bus stop. _Shit shit shit shit_. _Now I'm going to be late to work_ she thinks to herself. Blair starts to go through her book bag to look for her wallet. When she finds it, she notices that she doesn't have enough money for a cab back to the loft. She puts her face in her hands and takes a deep breath. Blair hears a car pass her, but doesn't look up from her current position. Suddenly, a car door slams, which makes Blair look up. What she sees surprises her. Chuck Bass approaches her, dressed ostentatiously as per usual and with a smirk on his face. When he is standing right in front of her he says, "You're Blair Waldorf, right? Is everything alright? You don't look so good."

"Yeah, I'm fine. I just missed my bus home and now I have no way to get back. I can't miss work either, because I can't lose this job," Blair responds.

Chuck looks at her before saying, "Look, I don't mind giving you a ride home. You can just come into my limo. Where do you live?"

Blair perks up as she replies, "Really?! You would totally be a life saver. And I live all the way in Brooklyn. Is that alright?"

Chuck looks at her disbelieving for a moment before replacing his expression with a slight smile and says, "Of course that's alright. I just forgot that you were from Brooklyn. You seem like you fit in well here at the Upper East Side."

"Oh, well thanks I guess. But Brooklyn is where I feel at home," Blair responds as she steps into the limo.

Blair sits down in her seat as Chuck makes his way to the driver to tell him her address. When he slips into the limo, he sits uncomfortably close to Blair. She tries to scoot to give him more space, but he doesn't allow it. She feels the car begin to move as she tries to move away from Chuck again, unsuccessfully. They sit silently for a few minutes before he finally speaks. Chuck says, "You know you're so hot, Blair. What would you say to a night out with me? I can guarantee it would be a night you would never forget," he says with a sly smile.

Dan's face suddenly flashes into her mind, but just as quickly as it comes, it leaves. "Thank you, but I'm not interested," she replies.

With the same sly smile on his face, Chuck says, "Why is there someone else? Because I can promise you that you'll forget all about him after a night with me."

Blair takes a moment to compose herself before responding, "I really am flattered. But there is no one else because I have no time for a relationship. So, no thank you."

Chuck laughs lightly before saying, "Who said anything about a relationship? I just want one night with you," he says as he moves impossibly closer to her. Blair can feel his hot breath on her neck as he says, "If there is no one else you're interested in, what's holding you back?"

Blair shoves him away as she responds, "I'm not the kind of girl who just sleeps around. So get that idea out of your mind, because we're never going to happen!"

He moves right back to her side and he grabs her arm. Chuck says, "I've wanted you for a while, and let me tell you something. I always get what I want."

Blair can feel his hand tightly gripping her arm as she tries to yank it away unsuccessfully. "Chuck let go of me," she says forcefully. He tightens his grip for a moment before dropping her arm. She looks down and can already see bruises beginning to form. She lightly touches her arm and winces quietly.

Chuck looks at her before turning to his driver and saying, "You can actually stop here. Blair can walk the rest of the way." The limo pulls over to the side of the road and stops.

Blair looks at him incredulously before saying, "You're an asshole, Chuck."

"I've been called worse things," he says with a smirk.

Blair grabs her things and opens the door. She walks out and begins to make her way home. She starts walking when she sees the limo pull up next to her. One of the windows goes down, and Blair looks at Chuck. He says to her, "I meant what I said when I told you I always get what I want."

Blair feels herself flush angrily before replying, "Well you can forget about it. There is no chance at all, especially after what just happened. So goodbye, Chuck." She turns away and starts walking home. Blair watches the limo speed away right in front of her as she feels her tears start to make their way down her face. She brushes them away angrily as she continues her walk. Luckily, she only had to walk about twenty more minutes before she made it home. She ran inside the loft, changed quickly, and ran to work, arriving only five minutes late.

She puts on her apron in the back when she glances down at her arm. She sees a dark bruise forming, obviously in the form of a hand. _God, I'll have to start wearing long sleeves until this goes away. Nobody can know what happened._

* * *

Dan returns to his apartment. _What a night!_ he thinks to himself. He goes into his room and picks up his phone to call Blair. He hears it ring a few times before it goes straight to voicemail. When it's time to leave a message, Dan says, "Hey, Blair! I'm guessing you're either sleeping, or maybe you're just coming home from work. But I wanted to let you know that tonight was great! But you didn't tell me that you were a huge fan of Vampire Weekend! When I told Serena the plan, she told me that you always tried to get her to listen to them, but she never would. You should have told me that! Next time, I will definitely get you a ticket also. Anyways, I hope you had a great night. Thanks so much for all of your help! You really are the best. See you later!"

Dan hangs up the phone and goes over to his bookshelf and pulls out his notebook. Suddenly feeling inspired, he begins writing a story, a story about a girl from Brooklyn and a boy from Manhattan.

**A/N: Hello, readers! Thank you so much for your lovely reviews! :) they definitely keep me motivated to keep writing! I hope you enjoyed this chapter. I had some issues with how to write about Chuck, so I hope it turned out all right! Enjoy, and keep the reviews coming!**


End file.
